Conan O’Brien’s Unrequited Fanboy Love for Robert Caro

WEST HOLLYWOOD, Calif. — Conan O’Brien, the longest tenured late-night TV host, has had them all in his 25 years on the air. Oscar winners. Hall of Famers. Bowie, Springsteen, McCartney.

But there’s one person who keeps saying no — someone whose work has been a near-obsession for the host for some time.

“At a certain point, I have the power to book a lot of people,” Mr. O’Brien said over dinner at Lucques, a Mediterranean-inspired restaurant here. “I’ve been around long enough. There’s a point where you feel like you’ve met everyone. Everyone. And then there’s Robert Caro.”

For years Mr. O’Brien has tried to book the Pulitzer Prize-winning author of “The Power Broker” and the multivolume epic “The Years of Lyndon Johnson.” And for years Mr. Caro has said no.

Mr. O’Brien, 55, started to realize his love for the biographer-historian was perhaps unrequited some eight years ago.

At the time, he had recently made the move to TBS after 17 years as a late-night host at NBC — a run that had come to an end with his brief stint behind the desk of “The Tonight Show.” Newly ensconced at “Conan” in the lower-stakes environs of basic cable, he had the freedom to give serious airtime to guests who would have gotten five-minute segments during his network days.

“We’re talking about authors, and I’m thinking, ‘Let’s get Robert Caro on — I’ll do two segments with him,’” Mr. O’Brien said. “The request went out. It was the equivalent of putting a penny in a well and never hearing the splash.”

Later invitations also resulted in polite refusals.

“The Path to Power,” the first installment of Mr. Caro’s biography of President Johnson, was published in 1982, when Mr. O’Brien was a student at Harvard. He received the book as a Christmas present from his father and soon fell under its spell, as did his roommate, Eric Reiff. They shared their new enthusiasm during a trip away from campus.

“Think of two guys in college going on a road trip,” Mr. O’Brien said. “You think about how we get a bunch of beer, we go to Fort Lauderdale, we get hammered. No. We go to a quiet beach in Rhode Island and we’re lying there and yelling at each other back and forth about Lyndon Johnson. ‘It was his father! His father had been disappointed!’ ‘But what about Pappy O’Daniel?’”

The later works in the epic series, which have been published at a rate of roughly once a decade, have more than lived up to the promise of the first, in Mr. O’Brien’s view. Mr. Caro, 82, has said he is closing in on completing the fifth and final volume, and the pompadoured comic is among those eagerly awaiting its publication.

“The Lyndon Johnson books by Caro, it’s our Harry Potter,” Mr. O’Brien said. “If there were over-large ears and fake gallbladder scars that we could wear instead of wizard hats while waiting in line to get the book, we would do it.”

After having been rejected numerous times, Mr. O’Brien came up with a plan to land his prey: a relatively sober streaming interview program called “Serious Jibber Jabber.” Guests have included the best-selling nonfiction author Michael Lewis, the historian Evan Thomas and the data journalist Nate Silver.

“I pretty much made this thing as a bear trap to catch Robert Caro,” Mr. O’Brien said. “I keep getting other people who are great. But no Robert Caro.”

The host sent word that he would be willing to interview the author in his hometown, New York City. No dice, Mr. Caro replied through an intermediary. Mr. O’Brien then asked him to dinner, without cameras. Maybe next time.

A onetime writer for “The Simpsons” and “Saturday Night Live,” Mr. O’Brien is one of the brainiest people in late night, even if he favors a loose, absurdist brand of comedy that has little in common with the topical style of Stephen Colbert, John Oliver, Trevor Noah, Seth Meyers and Samantha Bee.

Mr. O’Brien arrived at the restaurant for our interview carrying a sheaf of notes filled with dates and facts tracing his obsession. It included the time he attended a Caro reading at the Barnes & Noble in Union Square around the release of “Master of the Senate,” volume three in the L.B.J. series.

“I’m just checking,” Mr. O’Brien said, flipping through his notes, when asked what year he saw Mr. Caro. “I want to make sure I have as many answers as I can for you.”

It was 2002. Mr. O’Brien did not introduce himself.

“I don’t want to bother Caro and go up to him and say, ‘Of course, you must know me from the Masturbating Bear and Triumph the Insult Comic Dog, who will poop on you,’” he said, referring to comedy bits that were staples of “Late Night With Conan O’Brien,” the NBC show he hosted from 1993 to 2009.

Mr. Caro’s penchant for leaving nothing out — the still-growing L.B.J. series runs to more than 3,000 pages — is a quality that has wearied his detractors while inspiring special devotion among fans like Mr. O’Brien.

“One of the things that makes him one of the greatest biographers of all time is he’ll write about Lyndon Johnson, but when he encounters another character who’s interesting — Coke Stevenson — he will drop everything and go down deep, incredibly deep, into, ‘Who is this man really?’” he said. “He’ll find all this deep rich ore, which, once you know it, it’ll make the whole story that much more powerful. Whereas other people would dispense with those characters in a paragraph or two.”

Mr. O’Brien was insistent that Mr. Caro’s team has been nothing but polite in sending its regrets. In fact, a few years ago, Mr. O’Brien received a signed copy of “The Path to Power” with the inscription: “To Conan O’Brien. From A Fan — Robert A. Caro.”

Mr. Caro has appeared on other programs over the years, including “The Colbert Report,”“CBS This Morning” and “The Daily Show” in its Jon Stewart iteration. When asked for this article why he had yet to appear on “Conan,” the author said in a statement: “‘Conan’ — You mean it was O’Brien? I thought it was The Barbarian.”

Paul Bogaards, a spokesman at Knopf, Mr. Caro’s publisher, said of Mr. O’Brien’s many entreaties, “Suffice to say, his people have been in touch a few times (email, phone, Conan standing outside the building), and we remain cautiously optimistic about Caro making an appearance on the show before the decade is out.”

The refusals have done nothing to lessen the host’s affection for the author. “The biggest thing I want to stress is that my inability to get him to sit with me only makes me respect him more,” Mr. O’Brien said.

In his morbid fantasies, he imagines Mr. Caro appearing on “The Tonight Show Starring Jimmy Fallon,” where the guests often play games with the host.

“I know that someday I’m going to turn on Fallon and see Caro playing Pictionary,” he said. “And I’m just going to be enraged. He’s going to get everyone cheering, and Cardi B’s there, high-fiving him. And I’m just going to be enraged.”

As he continues his quest, Mr. O’Brien said he will draw on what he has learned from Mr. Caro’s epic series. “Like Johnson, I have an incredible drive and a complicated relationship with my father,” he said. “I’ll stop at nothing.”